KR890006567A - 설폰아미드 유도체 - Google Patents
설폰아미드 유도체 Download PDFInfo
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- KR890006567A KR890006567A KR1019880013280A KR880013280A KR890006567A KR 890006567 A KR890006567 A KR 890006567A KR 1019880013280 A KR1019880013280 A KR 1019880013280A KR 880013280 A KR880013280 A KR 880013280A KR 890006567 A KR890006567 A KR 890006567A
- Authority
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- South Korea
- Prior art keywords
- formula
- hex
- heptan
- enoic acid
- compound
- Prior art date
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- 229940124530 sulfonamide Drugs 0.000 title claims 2
- 150000003456 sulfonamides Chemical class 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims description 12
- KPSZWAJWFMFMFF-UHFFFAOYSA-N hept-5-enoic acid Chemical compound CC=CCCCC(O)=O KPSZWAJWFMFMFF-UHFFFAOYSA-N 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 238000000034 method Methods 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- ZJMCFPNLQOAANJ-RQOWECAXSA-N (z)-7-[3-[(4-methylphenyl)sulfonylamino]-2-bicyclo[2.2.1]heptanyl]hept-5-enoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1C(C\C=C/CCCC(O)=O)C2CCC1C2 ZJMCFPNLQOAANJ-RQOWECAXSA-N 0.000 claims 3
- -1 3-tosylaminobicyclo [2.2.1] heptan-2-yl Chemical group 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- XUDOZULIAWNMIU-UHFFFAOYSA-N delta-hexenoic acid Chemical compound OC(=O)CCCC=C XUDOZULIAWNMIU-UHFFFAOYSA-N 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 206010061216 Infarction Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000007536 Thrombosis Diseases 0.000 claims 2
- 125000000539 amino acid group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 230000007574 infarction Effects 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- ZSHWMGLGHMZHBP-RQOWECAXSA-N (z)-6-[3-[(4-bromophenyl)sulfonylamino]-5-bicyclo[2.2.1]heptanyl]hex-5-enoic acid Chemical compound C1C2C(\C=C/CCCC(=O)O)CC1CC2NS(=O)(=O)C1=CC=C(Br)C=C1 ZSHWMGLGHMZHBP-RQOWECAXSA-N 0.000 claims 1
- JAKDHRLDSNWWCL-HYXAFXHYSA-N (z)-6-[3-[(4-methylphenyl)sulfonylamino]cyclopentyl]hex-5-enoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1CC(\C=C/CCCC(O)=O)CC1 JAKDHRLDSNWWCL-HYXAFXHYSA-N 0.000 claims 1
- 208000030090 Acute Disease Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 1
- HQMLIDZJXVVKCW-REOHCLBHSA-N L-alaninamide Chemical compound C[C@H](N)C(N)=O HQMLIDZJXVVKCW-REOHCLBHSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 1
- HKXLAGBDJVHRQG-YFKPBYRVSA-N L-lysinamide Chemical class NCCCC[C@H](N)C(N)=O HKXLAGBDJVHRQG-YFKPBYRVSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 235000004279 alanine Nutrition 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 235000013922 glutamic acid Nutrition 0.000 claims 1
- 239000004220 glutamic acid Substances 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- OVGWMUWIRHGGJP-WTODYLRWSA-N (z)-7-[(1r,3s,4s,5r)-3-[(e,3r)-3-hydroxyoct-1-enyl]-6-thiabicyclo[3.1.1]heptan-4-yl]hept-5-enoic acid Chemical compound OC(=O)CCC\C=C/C[C@H]1[C@H](/C=C/[C@H](O)CCCCC)C[C@H]2S[C@@H]1C2 OVGWMUWIRHGGJP-WTODYLRWSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/005—Analogues or derivatives having the five membered ring replaced by other rings
- C07C405/0075—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a condensed ring system
- C07C405/0091—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a condensed ring system which is bridged condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/20—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Epoxy Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도, 제2도 및 제3도는 기니아 피그(guinea pig)를 대상으로 하여 STA2에 의해 유도된 혈합 증가를 본 발명의 화합물이 경과된 시간에 억제하는 비율의 변화를 도시한 것이다.
Claims (13)
- 일반식(Ⅰ)의 설폰아미드 유도체, 이의 사이클로 텍스트린 클라트레이트, 또는 R11이 수소원자이거나 NR13R14가 아미노산 잔기인 경우 그의 비-독성 염.상기식에서, R1은 (ⅰ) COOR11(ⅱ) CH2OR12또는, (ⅲ) CON13R4[여기에서, CHR11은 수소원자, 탄소원자수, 1 내지 20의 알킬 그룹, 탄소원자수 1 내지 4의 알킬 또는 알콕시그룹 또는 할로겐 원자로 치환되거나 비치환된 카보사이클 환, 또는 스테로이드이고, R12은 수소원자 또는 COR15이며, R13및 R14는 각각 수소원자 또는 탄소원자수 1 내지 4의 알킬 그룹이거나, NR13R14는 아미노산 잔기 또는 헤테로사이클 환을 나타내거나, R15는 탄소원자수 1 내지 4의 알킬 그룹, 또는 페닐 그룹이다]를 나타내며,은 탄소원자수 1 내지 4의 알킬렌 그룹이고, R2c은 수소원자, 탄소원자수 1 내지 4의 알킬 그룹, 또는 할로겐 원자이며, 일반식(C)에서 C5와 C6사이의 이중결합의 배위는 시스 또는 트란이스다]을 나타내고, 단,가 일반식(A)을 나타내는 경우, R11은 수소원자 또는 탄소원자수 1 내지 20의 알킬그룹이 아니다.
- 제1항에 있어서,가 일반식(A)을 나타내는 유도체.
- 제2항에 있어서,가 일반식(Aa-1)을 나타내는 유도체.
- 제3항에 있어서, (5Z)-7-(3-토실아미노비사이클로[2.2.1]헵탄-2-일)헵트-5-엔아미드, (5Z)-N-메틸-7-(3-토실아미노비사이클로[2.2.1]헵탄-2-일)헵트-5-엔아미드, (5Z)-N, N-디메틸-7-(3-토실아미노비사이클로[2.2.1]헵탄-2-일)헵트-5-엔아미드, (5Z)-7-(3-토실아미노비사이클로[2.2.1]헵탄-2-일)헵트-5-에노산과 피롤리딘의 아미드, (5Z)-7-(3-토실아미노비사이클로[2.2.1]헵탄-2-일)헵트-5-에노산과 알라닌의 아미드, (5Z)-7-(3-토실아미노비사이클로[2.2.1]헵탄-2-일)헵트-5-에노산과 알라닌의 아미드, (5Z)-7-(3-토실아미노비사이클로[2.2.1]헵탄-2-일)헵트-5--에노산과글루탐산의 아미드 또는 (5Z)-7-(3-토실아미노비사이클로[2.2.1]헵탄-2-일)헵트-5-에노산과 리신의 아미드인 유도체.
- 제1항에 있어서,가 일반식(B)을 나타내는 유도체.
- 제1항에 있어서,가 일반식(Ab-1) 또는 (Ab-2)을 나타내는 유도체.
- 제5항에 있어서, (5Z)-6-[3-(4-브로모벤젤설포닐아미노)사이클로펜틸]헥스-5-에노산, (5Z)-8-[3-토실아미노비사이클로펜틸]옥트-5-에노산, (5Z,7Z)-8-[3-토실아미노비사이클로펜틸]옥트-5,7-디에노산, (5Z)-6-[3-(4-브로모벤젤설포닐아미노)사이클로헥실]헥스-5-에노산, (5Z)-6-[6-(4-브로모벤젠설포닐아미노)비사이클로[2.2.1]헵탄-2-일]헥스-5-에노산, (5Z)-7-[6-토실아미노사이클로[2.2.1]헵탄-2-일]헵트-5-에노산, (5Z)-6-(4-브로모벤젠설포닐아미노)비사이클로[2.2.2]옥탄-2-일]헥스-5-에노산, (5Z)-6-[3-토실아미노사이클로펜틸]헥스-5-에노산, 메틸 (5Z)-6-[6-(4-브로모벤젠설포닐아미노)비사이클로[2.2.1]헵탄-2-일]헥스-5-에노에이트, 옥틸 (5Z)-6-[3-(4-브로모벤젠설포닐아미노)사이클로펜틸]헥스-5-에노에이트, 메틸 (5Z)-6-[3-(4-브로모벤젠설포닐아미노)사이클로펜틸]헥스-5-에노에이트, 에틸 (5Z)-6-[3-(4-브로모벤젠설포닐아미노)사이클로펜틸]헥스-5-에노에이트, 이소프로필 (5Z)-6-[3-(4-브로모벤젠설포닐아미노)사이클로펜틸]헥스-5-에노에이트, 멘틸 (5Z)-6-[3-(4-브로모벤젠설포닐아미노)사이클로펜틸]헥스-5-에노에이트 또는 (5Z)-6-[3-(4-브로모벤젠설포닐아미노)사이클로펜틸]헥스-5-앤아미드의 유도체.
- 제1항에 있어서,가 일반식(C)을 나타내는 유도체.
- 제8항에 있어서,구조식(Ac-1), (Ac-3), (Ac-4), 또는 (Ac-7)을 나타내는 유도체.
-
- 일반식(Ⅱa), (Ⅱb), (Ⅱc) 또는 (Ⅱd)의 화합물을 비티히 반응시키거나, 일반식(Ⅰb)의 화합물을 아미드 형성 반응시키거나, 일반식(Ⅰb)의 화합물을 에스테르화시키거나, 일반식(Ⅰd)의 화합물을 환원시키거나, 일반식(Ⅰe)의 화합물을 아실화시키거나, 일반식(Ⅲa)의 화합물을 설포닐화시킴을 특징으로 하여, 일반식(Ⅰ)의 화합물을 제조하는 방법.상기식에서,, R1, R11, Xb, R2b, R1c, Lc은 제1항에 정의한 바와 같고,은 제1항에 도시된 구조식(Ab-1) 또는 (Ab-2)를 나타내고,은 제1항에 도시된 구조식 (Ab-3) 또는 (Ab-4)를 나타내며, Xb1은 결합 또는 메틸렌 그룹을 나타내고, 단, Xb1및내의 질소원자는 환에 Syn으로 결합하여, Xb2은 Xb와 동일한 의미를 가지고, 단 Xb2및내의 질소원자는 환에 anti로 결합하여,는 일반식(A) (B) 또는, (C)를 나타내고, R11''는 탄소원자수 1 내지 8의 알킬 그룹을 나타낸다.
- 약제학적 담체 또는 제피제와 함께 활성성분으로서 유효량의 제1항에 따른 일반식(Ⅰ)의 화합물중 적어도 하나, 또는 이의 사이클로댁스트린 클라트레이트, 또는 R1이 수소원자인 경우 이의 비-독성 염을 함유함을 특징으로 하는, 고혈압, 혈전, 뇌졸중, 천식, 심장 경색, 협심증, 뇌경색, 및 급성 질환의 예방 및/또는 치료용 약제 조성물.
- 유효량의 제1항에 따른 일반식(Ⅰ) 화합물, 이의 사이클로택스트린 클라트레이트, 또는 R1이 수소원자인 경우 이의 비-독성 염을 경구, 직장, 또는 비경구 투여함을 특징으로 하여, 고혈압, 혈전, 뇌졸중, 천식, 심장 경색, 협심증, 뇌경색, 및 급성 심장질환을 예방 및/또는 치료하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP?266501/87? | 1987-10-23 | ||
| JP26650187 | 1987-10-23 | ||
| JP?94546/88? | 1988-04-19 | ||
| JP?94545/88? | 1988-04-19 | ||
| JP9454588 | 1988-04-19 | ||
| JP9454688 | 1988-04-19 | ||
| JP63197180A JP2565746B2 (ja) | 1987-10-23 | 1988-08-09 | 新規な炭素環系スルホンアミド誘導体 |
| JP197180/88? | 1988-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR890006567A true KR890006567A (ko) | 1989-06-14 |
Family
ID=27307576
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880013280A KR890006567A (ko) | 1987-10-23 | 1988-10-12 | 설폰아미드 유도체 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JP2565746B2 (ko) |
| KR (1) | KR890006567A (ko) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2270438T3 (es) * | 1995-06-21 | 2007-04-01 | SHIONOGI & CO., LTD. | Derivados amino biciclicos y agonista de pgd2 que contienen los mismos. |
| ES2188928T3 (es) * | 1996-04-26 | 2003-07-01 | Shionogi & Co | Pastilla de liberador-rapido s1452. |
| ZA984040B (en) * | 1997-05-15 | 1998-11-20 | Ono Pharmaceutical Co | Benzenesulfonamide compounds |
| DK1249233T3 (da) | 1999-11-26 | 2008-11-17 | Shionogi & Co | NPYY5-antagonister |
| CA2404125C (en) * | 2000-03-20 | 2011-01-25 | Merck Sharp & Dohme Limited | Sulphonamido-substituted bridged bicycloalkyl derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4654357A (en) | 1985-08-09 | 1987-03-31 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane substituted sulfonamide prostaglandin analogs |
| NZ218115A (en) | 1985-11-18 | 1990-02-26 | Shionogi & Co | Bicyclic sulphonamides and pharmaceutical compositions |
-
1988
- 1988-08-09 JP JP63197180A patent/JP2565746B2/ja not_active Expired - Lifetime
- 1988-10-12 KR KR1019880013280A patent/KR890006567A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2565746B2 (ja) | 1996-12-18 |
| JPH02180862A (ja) | 1990-07-13 |
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